Portraits with Strangers

"Right then, it clicked for me. People are actually more up to it than one would think." -Omar Z. Robles


Meeting new people can be a scary thing. It’s not uncommon to see the portrait of a stranger pop up in my feed, in which I’ll usually share a story about who they are or how we met, or some variation of. Almost always I get feedback saying something like “I wish that I could just talk to people like that!” 

I think about it, and despite the fact that I’ve always been social I haven’t always found it easy to approach a total stranger and ask to take their portrait. So how does one go from taking sneaky street photos to straight up approaching a new face and having them pose for your camera? 

Now, I’d really like this to be a discussion, but I want to give you some of my own point of view as well as the view of a friend and fellow photographer. 

Below is a short interview I did with Omar Z. Robles. He’s a portrait, lifestyle & fine art photographer living in NYC.  I asked him a few questions and got some great answers! 


1.  When you decided you wanted to photograph people, and especially strangers, what were your initial thoughts and/or concerns?

In a certain way, it started as a challenge to myself. I was initially afraid to do it and since I really don’t like that feeling of keeping myself from doing something for no good reason…I just made myself do it. When I did, I found it to be so rewarding I just had to keep putting myself up to the challenge again.

I’ve been shooting street photography for about three years now, but that was strictly shooting candids. Shooting portraits of strangers however was a different thing. The idea of talking to strangers made me anxious unless it was for a job. However, I had been really inspired by Ruddy Roye’s work for some time. After meeting Ruddy and befriending him, I’d say his energy really inspired me to overcome my anxiety about taking to strangers. Once again, it proved to be an amazing experience.

2. When you decided to go for it and approach that first new face, what did you have to fight to make yourself do it?

I woke up really early one Sunday morning, sort of with the thought in my mind but really fighting it in a way. I saw a man walking towards me with a large hat and a black feather boa on his neck…my first thought was, "if you don’t ask him…you’re and idiot." So I did, and to my surprise he said "yes", and didn’t even ask what was it for. Right then, it clicked for me. People are actually more up to it than one would think, if you have the right attitude of course.

3. As you’ve done more and more portraits, what have you seen change in the final outcome of the photos themselves?

I don’t really feel the photos themselves have changed, but I know I have. Each and every time I feel more at ease and I find myself having longer conversations, hence enjoying the experience beyond the image itself.

4. I’m certain that you’ve been a part of and learned a lot from meeting these folks. Any favorite stories?

Not long ago, I was shooting street candids when I see these two old gentlemen on Soho, one of them with a very distinct beard. I took their picture as they were talking. One of them noticed and told the other. The bearded man came over and asked me to delete the picture. The other walked over and said “actually I don’t mind it at all, let me see it”. After which, he asked for another picture posing with his friend. He followed by saying:

- "You know a few years back I wouldn’t have let you take my picture." -"Why is that, I asked." -"Cause I was a mobster.."

5. Do you have any go-to posing or backdrop techniques you’d like to share?

Since I am shooting my current portrait series on Sunday mornings before most businesses open, I like using the rolling gates as backdrops. I try not to pose people too much since I try to be as fast as I can be in oder to let them go about their day.

6. What advice do you have for anyone wanting to step out and tap a new person on the shoulder for a picture?

Breath, go out and just think about doing one…and then repeat, and keep repeating. Once you start, you’ll get a momentum…the important thing is to get the ball rolling, after that is downhill from there.


Below are a few portraits that Omar sent over to me. Be sure to check out his work and also be sure to check out his weekly "Sunday's Best Portraits"The best way to follow the series is on Momentage. (you can find both of us on there, and you should!)

Some very true words spoken by our friend, Omar. My own experience has had its own similarities. The thought of asking someone you've never once seen if you can share this intimate moment certainly can be intimidating, but Omar is right. There comes a point where you have to just do it. It does get easier the more you ask. 


Here are a few of my own tips:

Confidence is key. When you approach someone know in your own mind why you're approaching them and be prepared to share that. Make eye contact and be polite and direct. Watch your body language. If you are timid, mumble and shuffle your feet while staring at the ground you may not get as far. You may even do all of the when you first start, and if you do that's okay. Just keep on. 

Think of it like this... What's the worst that could realistically happen? Most likely someone being very offended, telling you to "bugger off" and call you a "so and so".  Now, that is extreme, and even IF that were to happen... you loose nothing. Maybe your pride would take a little hit but that's about it. Just move along to the next person you find interesting. 

I have asked quite a lot of people to pose for a portrait, and I have been told "no" on several occasions, but to date no one had ever been rude. People are usually more curious than anything, and sometimes even flattered. You'd be surprised how caring enough about them to take their photograph brightens their day. Also, you get to meet and share some amazing stories, like the ones that Omar has shared with us. 

One of my own... Last year I was sitting in a coffee shop in the Northwest. I happened to see a very tall and very dapper gentleman walk in. He was older, and had a certain Dos Equis vibe about him. I watched as he ordered his americano  and thought about how much I'd like to photograph him. I tossed around weather or not I should approach this gentleman, and as he was walking out the door with his brew I said to myself the same thing Omar said to himself. "You're an idiot if you don't at least ask!". So I did. I ran out the door behind him, caught up and tapped him on the shoulder. I remember being very forward and honest with him. I shook his hand, introduced myself, telling him I was a photographer, and then said "I couldn't help but notice you in the shop. I thought to myself "A man that takes the time to dress as you do must have an interesting story." I'd love to take your portrait if you don't mind." 

That man's name was Vince Brown, and that little interaction ended up with me spending 3 hours at his home just getting to know him and having genuine amazing conversation. He made me some of the most excellent coffee I've had to date, which was of course highlighted by the experience, and we spoke of everything from food to philosophy, and from vinyl records to motorcycles. I snapped one iPhone shot of Vince that day (pictured below) and later went back and did a full photo shoot.

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Just the potential for greatness alone makes it worth pushing yourself to say hello. Beforehand, you can't ever know for certain how someone will react or what will come of it but if you don't ever try you won't ever know. Once you get into it you may find that you're more social of a person than you ever imagined, and for me it's been a key of life. Building relationships will take you further and to places you couldn't have otherwise dreamed. Be open to new interactions. Keep your eyes open. Look for any reason to say hello. Not just for a photo, but for the simple sake of making a connection. When you walk past someone smile instead of averting your glance. Say hello to the person next to you in the grocery line, or when you're getting a cup of coffee. I challenge you to at least try it! 

Now, as I said, I would love to see this turn into a discussion. I'm interested! Do you have stories to share? Techniques you use and would like to pass to others? Questions you'd like answered? Let's hear em! 

Best,

Chris